A couple of years ago while watching a documentary I discovered a house cat can revert to its natural state under the right circumstances. I imagined my obese ginger male going from his prescription canned cat food to hunting and feasting on rodents and birds. His once silky coat now matted with dirt and leaves. His fat haunches transformed into lean muscle. Instead of dramatically crying for his supper twice a day, he’d hide in alleys and beneath parked cars avoiding contact with humans while ruling the night. As I stroked Otto’s fur I decided I’d was no longer single, I’d turned feral instead.

When I went through a difficult divorce nine years ago I suspected my dating life would be difficult. I had no idea it would become a soul-crushing, near impossible endeavor. Right out of the gate, I had two fairly tragic rebound relationships that imploded almost as soon as they’d started. Online dating felt more like an exercise in attrition and increasingly lowered expectations. I’d get the obligatory emails from men involved with BDSM – twice as many submissives than dominants. Couples would email me hoping I want to join in some three-way play. My inbox would overflow with email from men in other countries and far away states. Traveling business men would contact me late at night, expecting me to drop everything to run to their hotel room and be their unpaid prostitute. Dates rarely materialized and if they did they were often two awkward people sitting across from each other with nothing in common but judgmental stares. Men openly criticized me for my profession, the circumstances around my divorce, and pretty much every lifestyle choice I had made up until the point of meeting them. When I met men offline it seemed like the only interested parties were either married or so young they could easily be mistaken for my son. I’d also met guys who expected me to go home with them five minutes after meeting them. If I showed any hesitation at all I was quickly forgotten for the next random woman who would say yes.

When I showed interest in anyone I was usually treated like a completely crazy person. I realize I’m not every man’s dream woman. I have a big personality. I talk a lot. I’m so nerdy that I can blather for hours about the rise of fascism or the madness of Kaiser Wilhelm II. I won’t know anything about the latest movie that came out but I could tell you more than you’d ever want to know about the life of Nikola Tesla or how mutations take hold in a genome. I’m opinionated and stubborn. I will disagree and challenge men often and openly. For amusement I get onstage and yell at total strangers in darkened basements that are masquerading as makeshift comedy clubs. I’m a sledgehammer of truth. Some folks find my qualities charming while others, find them incredibly annoying. My natural nemesis seems to be the classic khaki wearing, boat shoed finance bro alpha male. On multiple occasions I’ve found myself in screaming matches with a half drunk, angry day trader minutes after meeting them.

I’m also not all that interested in finding my dream man. I have massive trust issues and pretty much assume every man is lying to me from the moment they open their mouth. Because my ex-husband was a closeted gay man I pretty much assume all men are gay until proven otherwise. Any nurturing qualities left in me were stamped out by my dysfunctional and broken marriage. I don’t want to fix a man, pay his rent, make him forget his last girlfriend or guide him through rehab. If he’s not ready to wear I’ll just toss him back on the pile. I have zero interest in being an unpaid and untrained psychotherapist. There’s no part of me that longs to hang out with people I can’t stand because they’re friends with my partner. I don’t want to sit through plates of hot wings and beer when I’d rather have vegetarian Chinese takeout. If he’s wounded and broken, I’ll leave him for someone who can handle wounded and broken. I’ve got a freight train worth of emotional baggage and a hair-trigger that will cause me to bolt the second I sense danger. If a man blanks me on a text, I will delete them from my phone.
I’ll leave my apartment with glasses, messy hair, ball caps and dirty jeans. No fucks are given. I watch my weight like a hawk because I have to for my industry but I honestly don’t care if someone finds me “pretty.”

I’ve got no online dating profiles. I waste no glances as men walk by. I pose no questions about a man’s dating status.

I live in an apartment the size of an average single car garage. My 450 square foot space is so small that no man would look at it and see an inch for his belongings. There’s no spare drawer or extra closet space. If I was actually trying to date I’d issue parking rules on my front door. – Four hour minimum or mandatory tow.

I look forward to my future as I grow increasingly strange and eccentric. I’ll become the 60-year-old with blue hair who still wears Doc Martens and has birthday parties for my cats. The lack of companionship has caused entire sections of my personality to atrophy and die. I encourage others now to eschew the label of single and embrace the feral mindset. We are no longer waiting for our Mr. or Mrs. Right, we are hunting proverbial birds and mice in the night and loving every second of it.

Last week a debate about what constitutes sexual assault and what doesn’t erupted on social media. I won’t rehash the horribly written article about Aziz Ansari and I won’t hyperlink to it either. That site has gotten plenty of traffic in the past week. I don’t want to debate the language, tone or content of the piece. Whatever could be said about it has been said about it. I’ve officially reached Aziz fatigue.

What I do want to continue however is the discussion about the weird grey area that exists between enthusiastic obvious consent, and less than thrilled uneasy consent. This is a very real problem for both genders, although women have been conditioned to accept it more so than men. Most of us have been there. We agree to do something sexually that we’re not sure we want to do. Again, I’m not referring to the Aziz article or anything in it, I just wanted to explore what many of us talked about in discussions about awkward sexual experiences. In a perfect universe we should strive for obvious enthusiastic consent, but we’re also not going to get rid of hundreds of years of social conditioning overnight. We are currently in a strange new world where some of the shame and stigma regarding human sexuality has been lifted, while still living with outdated perceptions of gender norms and what constitutes appropriate behavior.

The most compelling insight on the piece came from a surprising source – the sex positive community. I have a few friends who are so sex positive they have orgies for fun. They plan sex parties for a living. Many of them are in polyamorous or non-monogamous relationships with multiple partners sometimes of both genders. Some of them have worked as strippers, prostitutes, dominatrixes and even sexual surrogates. They speak of their sex lives as easily as most of us would talk about our pets or hobbies. They openly brag about having over 100 sexual partners or more. The general tone that I got from nearly all of them was.

What we have here is a lack of communication.

For decades it’s been drilled in our heads that we are not supposed to talk about sex. Human sexuality is rarely something we have frank and open conversations about, at least with new sexual partners. We are fed a myth our entire lives that amazing sex can be had with total strangers with very little communication. The exact opposite is true.

Sex is like rocket fuel to humans. It’s so important to us it’s literally how we create human life, yet at the same time we try to treat it like it’s something we can engage in without a second thought. Of course we can but we need some ground rules with a new partner if that’s going to happen. No one would think to jump out of an airplane without first being shown how to use a parachute. I don’t know why we can think we can magically enter into highly emotionally charged situations without figuring out appropriate boundaries first.

This list is about some of the strategies a person can use to avoid awkward, clumsy and uncomfortable consensual sexual encounters.

Everything on this list with a couple of exceptions is meant for BOTH GENDERS. Although I wrote this with straight couples in mind, some of the same principles could be applied any sexual orientation or gender identification.

*This list is only in regards to consensual sexual encounters. No amount of communication will deter a sexual predator. In those cases the only thing a person can do is physically fight back, escape a situation or scream for help if that’s an option. I want to make this distinction now as I don’t want anyone to think a person can simply talk their way out of a sexual assault. I speak about this as a survivor of sexual assault myself. Sexual assault is a criminal act where one half of the situation is given no agency, no control, no voice and no choice.

Tips for avoiding awkward sexual experiences.

Ask for what you want.

There is nothing wrong with simply asking for what you want. Both partners should be direct and open about boundaries and comfort levels.

The phrase “Do you want to have sex?” can be very sexy. It’s also incredibly unambiguous. The phrase “Can I kiss you?” can also be smolderingly hot if said in the right situation. It’s also perfectly acceptable to say what you don’t want. The best way to do this is to use clear language that cannot be misunderstood. Words like “No” “Stop” or “I don’t want to do this” are hard to misinterpret. Again this goes both for men and women. Men also find themselves in situations where they are not comfortable. Neither partner can assume the other one knows what they want without direct communication.

You are NEVER obligated to do anything you don’t want to do.

It doesn’t matter how much someone spent on a date. It doesn’t matter what you’ve already done on a date. Making out doesn’t mean you consent to oral sex. Having oral sex doesn’t mean your consent to anal sex. Having anal sex doesn’t mean you consent to new partners being added to the mix. If you don’t want to reciprocate or you’re not feeling it you can say no. You can stop at any time in the date. It might be awkward or strange to end the date abruptly, but the momentary awkwardness will be easier in the long-term than going through with something you’re not sure you want to do.

You don’t have to be polite if you don’t want to do something.

This is the only guideline on this list that is directed at women more than men. As women we are programmed almost from birth to be nice, sweet and accommodating. When you enter into a sexual act you are kind of putting yourself on the edge of a proverbial cliff. You don’t really know how your partner might treat you or react. During a sexual encounter a human being is about as vulnerable as they are ever going to be. This is not the time to worry about being polite. If you are freaked out or scared, you can just let it all out. No need to worry about how you’ll be perceived. Speak your truth. Stand up for yourself. If someone expects you to have unprotected sex and you insist on using protection say NO as loudly and as strongly as possible. There is NO WAY IN HELL you should put yourself in a potentially medically dangerous situation just to seem nice.

Real life is not a porn movie.

Porn is probably the worst teaching tool for having great sex. In most porn scenarios next to no dialog is spoken. A man somehow just knows that it’s OK to do all sorts of violent and depraved things to a woman he’s just met, he might even include another male partner without even remotely checking in with the woman. This is of course a fantasy.

Real life is not a fairy tale.

You might get lucky and have some incredibly romantic near perfect dates that end in beautiful, connected, and full-filling sex with someone you barely know. It does happen. It’s quite rare. Most amazing sex happens with someone you know well and have been having sex for some time.

When in doubt – check it out

If you suspect your partner is not into something stop and ask them. One of the craziest stories I’d ever heard came from a friend of mine who told me that in the middle of sex a new partner smacked her across the face. She stopped him immediately and said, “What are you doing? Why are you doing that?” he claimed his last partner was really into it. My friend told him she wasn’t. He stopped. She never had sex with him again. Because he immediately stopped the behavior after she requested it, she doesn’t consider this sexual assault. It’s a great example of a man assuming she would like something his last partner enjoyed. These assumptions happen all the time with both men and women. It’s ALWAYS better to check in before you take the risk of entering into behavior that could be seen as predatory, violent or criminal.

If it’s bad early on, it will probably stay bad.

I hate to say it but you can tell a lot from a kiss. If a man or woman’s idea of a hot kiss is your idea of a disgusting one, you’ll probably never connect sexually. It’s fine to simply make up some excuse and get out of the situation before you find yourself in a much more awkward experience later that night. Everyone goes through this. If a partner looks great on paper and you like him or her otherwise but her or she repulses you sexually, you’re probably better off not taking things further.

Excessive alcohol use can blur your judgment.

What I just typed is common sense. What I just typed has also been labeled as sexist, regressive, abusive and part of rape culture. The problem with the simple statement of “Don’t get drunk” is it’s often only told to women. Of course women should be able to drink alcohol if they want to and even get drunk. This exact same advice should also be given to men. Just as it is far more difficult to drive a car or walk down stairs, it’s also much more precarious to enter into a sexual situation when we are severely intoxicated. No one is perfect and people will sometimes accidentally drink too much. The dangers of excess alcohol are just a good thing to remind yourself of if you’re about to go out with a total stranger. I want to stress this again. BOTH GENDERS should heed this advice.

Gender specific “rules” that should be thrown out the window

For women

Men won’t respect you or ask you out again if you have sex too quickly after meeting them.

Don’t go out with him if he asks you out with less than three days notice for a date

Don’t go home with a man on a first date.

Don’t make out with a man on a first date.

Tell him you’ve had three sexual partners in your past. (For most of us that would be a lie)

Don’t openly talk about sex or act interested in sex.

Never really say what you feel always play the game

(Many more rules/assumptions too many to list here – basically that women must remain virginal, pure or at least appear so. Women must also act coy, not be direct and constantly appear nice)

For men

If a woman goes home with you on the first date she wants to have sex

If a woman has sex with you on the first date she has less value

Any woman can be convinced to have sex with you if you just keep trying

If a woman has more than three sexual partners in her past she has less value

If a woman makes out with you that means she wants to have sex with you.

If a women dresses in a revealing manner she wants to have sex with you.

If a woman has joked or flirted with you that means she wants to have sex with you.

Never really say what you feel always play the game

(Many more rules/assumptions too many to list here but basically that men should pursue, pursue, pursue even when things seem pathetic. Basically the cliché of a boss chasing his secretary around the desk.)

These are all antiquated ideas about love and sex. Most of these “rules” leave both genders confused and frustrated. The best way a man can find out if a woman wants to have sex with him is to ask her directly. Even though it’s usually wise to avoid sex with perfect strangers, I’ve known several long-term loving relationships that started out just like that. We have to stop thinking in rigid terms of gender roles and old-fashioned codes of behavior. We have to smash the ideas of playing hard to get, acting like we don’t really want sex when we actually do, and generally blurring the lines of open communication. We have to speak up as openly and clearly as possible and empower ourselves to say no when needed. Again this goes for both men and women.

The last guideline really has nothing to do with awkward sex but is more about the flip side.

You can have great sex with people who are terrible partners

This is probably one of the toughest lessons in life that both men and women learn the hard way. I think all of my friends have had amazingly hot, passionate sex with people who were absolutely horrible to them. Sex is great, but if someone is really treating you like garbage outside of the bedroom you’re better off without them. You can always find another partner who you will click with completely who won’t emotionally abuse or neglect you.

I’ve read a lot of articles regarding this topic that were all saying the same things I’m saying here. This is also extremely obvious advice, I admit that openly. I just wanted to get this out in a way that didn’t seem preachy, use words like patriarchy, misogyny, toxic masculinity or any other ism. Even though this is a widespread problem that is deeply entrenched in our culture we don’t have to think in terms of lofty goals to solve it. It starts with each and everyone of us. If we all want to have good sex we just need to start talking to each other about everything and anything. Don’t feel weird asking questions and never assume you know what’s going on in anyone else’s head.

I’ve been single now for about eight years straight since my divorce. In that time I’ve had a few short-lived relationships but for the most part I’ve flown solo. I’ve discovered the hard way that the term “single” means a lot of different things to different people. This city is so large and so densely populated it seems some can’t help but constantly see a never-ending array of choices for potential partners. I’ve had so many men bold-faced lie to my face regarding this issue that I’m tempted to hand them a survey, and tape the entire exchange so when they say

I never said I was single

I won’t really do that but it’s frustrating that I feel like I have to ask questions like a prosecutor in order to get the truth out of some random dude on a date.

So what does it mean to be “single” in the city that never sleeps? I’m not including polyamorous or non-monogamous men in this list because they tend to be incredibly upfront and honest about their relationships status. This is for about the “single” boys who just like to blur the truth.

Single Single: You aren’t having sex with anyone on a regular basis. You try to date but nothing seems to work out. You mostly hang out with your friends and maybe watch porn.

Mostly Single: You are casually seeing someone. You’ve hooked up countless times, you socialize together and most of your friends consider you a couple. Although you’ve both being seeing each other on a regular basis for months neither of you like “labels” and you’re not sure if she’s having sex with other men or not. You take photos of your friend and post them on social media but never with yourself as a couple. Even though she’s met your parents and you’ve taken trips together she’s DEFINITELY NOT your girlfriend and as far as you’re concerned you’re 100% single. You flirt with other women and lead them on, but usually stop short of hooking up with them.

Single on Facebook Single: You’ve been dating someone for months now, you just haven’t bothered to change your relationship status update on Facebook yet.

Friends With Benefits Single: You’ve got a rotation of women that you text on the weekends and late at night for sex. You like them alright but you’re hoping none of them get too clingy or text you too much. All of these women know they aren’t the only one in your life and you are NOT serious about any of them. There’s one gal on your list who you tend to text more often and dump all your emotional garbage on them. For now she puts up with it. If she starts telling you too much about her life you’re out. You’re still hoping to find that perfect someone if she exists at all.

Tinder Single: You like to have sex with lots of women, but usually only once. Tinder is your favorite method of hooking up. You sometimes accidentally swipe right on a girl you’ve already banged. Things can get awkward. You’ve also learned it’s better to call women by a pet name since you’ll forget their name seconds after meeting them. They all become honey or babe to you, if you even bother to have a conversation before or after sex. You’re definitely single but single for life.

We Broke Up I Swear Single: You broke up with your girlfriend months ago but you’re both on a lease and finding a new apartment in tricky in Brooklyn. Neither of you would say you’re dating. You’ve even got a couple of roommates but since this is a three bedroom apartment, that means one of you has to sleep on the couch and there have been plenty of late nights when you’ve ended up hooking up again. You still fight so it’s a bad situation but it’s only temporary and for the moment you’re looking for love! Maybe you’ll end up moving in with your next girlfriend.

I’m totally over Her Single: The love of your life just left you. OK she didn’t just leave you it’s been almost two years but you’re TOTALLY over her. Sure you still have every photo you’ve ever taken together on your social media accounts, and yes you still constantly bring her up but you are TOTALLY over her. You still call her mom from time to time but her mom is a really nice woman. You’d do the same thing! Last weekend you helped her move into a new apartment and assembled most of her furniture. She knows she can call you at any time of the day or night but you are OVER HER. She’s a great and beautiful person and it just didn’t work out and you wish her nothing but the best.

I’m a Liar I’m not Single: You tell women you’re single because you want to have sex with them. You’re a married man or you’ve had the same partner for years and have kids with her. According to the tax code you’re single but by just about every other metric you are very much one half of a couple.

My category – Feral Single – I’ve been single for so long now I don’t know if it’s possible for me to have a relationship anymore. I LOVE living alone. I never want to compromise on anything or make any major decisions in my life again that involve another person. I’ve gone feral. Like a former house cat who was once fed and cared for I now survive by my wits. After a long hard day I come home vent on Facebook and talk to my cats. I’ve become the ultimate loner – self-sufficient, wily, and not likely to be tamed any time soon.

The situation goes something like this. I meet a guy who shows interest in me. A few have even invested quite a bit of effort and energy to win my favor. Just when I think I might be letting my guard down enough to actually bond with him, I find out about her. She might be an ex-girlfriend, an ex-wife, the mother of his child or the one who got away. She have helped destroy his marriage, or gone out with him on wild benders. She could have, slept with his best friend, stolen his money, joined a cult, realized she was gay, or stuck around in his life just enough to emotionally manipulate and abuse him. There are so many ways to become “her.”

I find a problem with “her” in nearly every middle-aged single man I meet. To be fair I’m sure plenty of women also obsess about a “him” from their past. It seems as we get older we become a patchwork of our former triumphs and traumas and can’t help but bring them to the next relationship. Our nostalgia and idealization of former lovers keep us trapped. Some men are more transparent about this than others. I’ve had the following happen to me while on first dates with men I barely knew.

One admitted his marriage fell apart because he was still in love with his former girlfriend. He never worked it out with the former girlfriend but his obsession destroyed his marriage.

Another said he was still angry at his last major girlfriend. Not so uncommon except he had dated her over 20 years before I sat across from him nibbling on tapas.

One said and I quote “I still love my ex-wife. My friendship is very close with her, even though she’s with someone else and if you or any other woman has a problem with that, I’ll always choose my ex-wife.” This might be understandable if they had children together but they did not, and she lived halfway across the country.

Another guy told me that he was still in love with his ex-wife, even though she had told him she “never wanted to have sex with him”, and she had left him for another man.

The worst one was a man I had dinner with who went on and on about another female comedian he had corresponded with on OKCupid. When he found out I knew her he said, “I find her fascinating and would love to have drinks with her.” I blocked him from my phone on my way home.

I even had a man ask me for advice on ways he could get his ex back. This was WHILE he was on a date with me. I honestly felt sorry for him, but give me a break.

Even in my first major relationship right out of the gate post-divorce, my partner openly pinned away for the woman he had just dated before me. She lived on the opposite coast and had never actually spent any significant time with him, but in his eyes she was somehow perfect. Because she was inaccessible she was without flaws, yet an available woman who actually wanted him would never measure up.

This happens so often that now when I meet new guys I almost want to just ask him,

“So where are the bodies buried when it comes to your ex? Do you hate her? Do you still love her? It doesn’t matter as hate and love are two sides of the same coin, so either way it’s bad. How many times do you talk to her in a given month? Are you actually divorced yet? Get it all out now, so I can leave before we might feel obligated to actually order dinner.”

When I see this pattern repeated it just reinforces every insecurity I have about myself. All of the following go through my brain at the same time

Why is he so obsessed with her?

Why is no one obsessed with me?

Why am I OK for a backup but never the primary woman in any man’s life?

Why do some men obsess over women who treat them like garbage?

Do men only want women that they can’t have?

Why would he still want her if she left him for another guy?

I’m not good enough. There’s something about me that makes me disgusting or unappealing.

Why did he chase me if he really wants her?

Would he take her back if she wanted to try again?

If I improved myself or changed my personality would that help?

What magic do these women posses?

I admit none of those thoughts are healthy or useful. It’s my neurosis going on overdrive. I find the constant struggle against “her” extremely demoralizing and a disaster for my self-esteem. I can logically tell myself it’s not me, the guy is just hung up on his ex, and he’d treat most women like this. I want to grab some of these men by both shoulders and scream

“She doesn’t want you anymore, let her go.”

“She’s so mean to you, you deserve better.”

“”If you think you guys still have a chance, then do everything you can to get her back, just leave me alone.”

The hardest are the men with children. I don’t have kids myself, so I honestly have no idea how strange an intertwined a relationship with an ex could get. Even if two parents absolutely hate each other they will still be deeply entrenched in each other’s lives for many years to come. So far I’ve encountered men who bend over backwards to keep their ex happy, and men who constantly battle with their ex over every decision involving their kids. Both are a nightmare for a new partner. If a man is spending all of his energy towards the ex there’s nothing left for anyone else.

This rarely happened in my 20’s. Men that age just didn’t seem to get as worked up about a former partner. It seemed like people were breaking up and hooking up with new partners all the time, without much second thought Once we get older and put much more investment into a relationship, it just gets harder to let go. When our own personal “Happily Ever After” story gets crushed, we have a hard time imagining a new one. In and ideal situation I would just pass out a psychological evaluation to every potential new partner with lots of questions about how they view their ex. I know that would never really work, but it would certainly save us both time and energy. *I’m not really serious, that’s sarcasm….but honestly it would make things easier.

I’ve lived in New York City now for fourteen years. I’ve been single for the past six, and I started searching for a co-op about a year ago. I couldn’t help but notice the eerie similarities between hunting for real estate and looking for love. Both are rare and precious commodities. New York City’s vacancy rate hovers around 3% and never goes above 5%. About 3/4 of all apartments are rentals, leaving only the remaining 1/4 available to buy. Most of the apartments on the market are co-ops that require financial gymnastics, and approval of an overly scrutinizing board. Even if you find an apartment in your budget you still have to get 80% financing and then impress upon your soon to be potential neighbors that you’re a low risk addition to their building.

Dating here is not much better, especially for single women. New York City has 150,000 more single women than single men. It might not seem like a huge number in a city of 8 million but it’s enough to throw off the odds a bit. To make things worse most New Yorkers work long hours, live scattered over five boroughs and have little disposable income to throw away at dating. I’ve found it’s best to not get too emotionally attached to any one partner or property.

I once was the only person to show up at an open house for a cute prewar newly renovated studio in prime condition. Just as I was about to start the long and arduous process of making an offer, an all cash buyer walked in before I had a signed contract and snapped the property out from under me. I watched in horror as the same scenario happened again with other properties. In dating, I’ve had a few amazing dates with men who seemed almost perfect only to have them vanish without explanation. My text messages went un-answered, my emails ignored and I never knew the reason.

I couldn’t help but see the similarities and the heartache that went with both, so I devised a glossary of sorts of common terms used in NYC real estate listings and how they equate with the dating scene in New York City.

Prime Location = Is the trip between Astoria and Bushwick worth it? Can a man in the Bronx find love with a woman in Staten Island? Is Queens to New Jersey even possible? Finding someone on the same subway line = prime location

Low Maintenance Costs = Cheap date

All Cash Buyer = Partners that offer everything up all at once with very little drama and no strings attached. The downside is they could flip you. Just as quickly as they find you attractive, they’ve moved on. They can just as easily make another offer as quickly as they made the first.

Unit has pre-existing long term tenant = Married.

Board Approval Required = Facebook, Instagram, Twitter, Snapchat, LinkedIn – everything dissected and analyzed for risk assessment. Are you friend’s with an ex? Is your job stable? Do you post NSFW videos, sports clips or cat memes? How many friends do you have? Are your tweets too personal or do you post political rants? Do you change your status update 20 times a day? Do you hardly ever check your profile? Are your photos of landscapes, or of your family

No Board Approval Sponsor Sale = The person either doesn’t know how to use the internet or doesn’t care. No questions asked as long as you fit the criteria. You are dealing with a risk taker or at last someone over 50 who doesn’t understand this thing called “the internet.”

Lack of Inventory = Are you a woman over 35? Then you know exactly what this means. Most men in your age group are married or at least coupled up. You’re going to have to look a lot harder for what you want, or settle for someone much younger or older. It’s not as a big of a problem for men. If you’re wondering why, it’s called babies, biological clocks and a patriarchal culture that values younger women over older. Although no one is immune, both genders can have unrealistic age standards when it comes to dating.

As impossible as the New York Real estate market is right now, I’ve had far more luck finding a new apartment, then a partner. Let me rephrase that for emphasis. I’ve actually had an easier time finding an affordable apartment in a year than I have finding a partner in the nearly six years I’ve been divorced. I’m not even kidding. In my search for an apartment I had the help of an attorney and real estate agent. I also looked EVERYWHERE from the far reaches of Brooklyn, to Queens, upper Manhattan and even parts of the Bronx. I called and emailed at one point about 25-30 agents and saw as much property as I could possibly fit into my schedule. There wasn’t much on the market in my price range but I viewed everything within reason.

I’ve basically tried the same approach to dating in that at this point I’ve probably been on at least 25-35 dates. Most have been awkward and painful and a few men have had full blown meltdowns. I’ve been out with men who complained about their ex-wives the whole time, bragged about their drug use, openly insulted me, or expected sex on the first date. The vast majority of emails I’ve gotten on online dating websites have been from men under age 25 or guys looking for no strings attached sex. Most of them men who do contact me never follow through with a date. So far nothing has worked, and I haven’t gone out with anyone for more than two or three dates in over five years.

For now, I’ll just settle for the apartment of my dreams rather than any prince charming. Real estate is more stable anyway, it won’t have a midlife crisis and leave me for a younger seller, develop a substance abuse problem, grow mean and bitter and blame me for all it’s shortcomings, develop a gambling or ignore me and go play golf. It may not cuddle at night but it will increase in value, and in the end I might get lucky and unload it to an all cash buyer. I certainly couldn’t ask for such certainty with a new boyfriend.

My whole real estate search also made me ask some questions about myself. I’m definitely a pet friendly unit with good financials and low maintenance, but one that needs some TLC. I’d also say my board is fairly strict and rather picky of any potential candidate but the opportunity for a long-term investment is solid. Now, if I could just find the right buyer, I’d be all set.

I written about this topic before, but after a long hiatus from online dating, I’ve decided to revisit it. It seems like men’s photos are getting worse, not better. As I’ve said on the blog multiple times, If I was going to give men any advice on how to create a successful online dating profile it would be this.

Have a trusted female friend look over your profile before you publish it.

I could type that 100 times for emphasis, but I’ll restrain myself. Don’t use your mom, or your sister, use a trusted female friend. You want to use a woman who doesn’t see you as a a nonsexual being, so your relatives are out of the question.

Here are my top 10 tips for picking the right photo for your online dating profile.

1. Don’t look like a serial killer – What does a serial killer look like? It’s hard to say really. It could be the outdated serial killer glasses, or the slicked down side part. We just know it when we see it. Show your friends, and simply ask – Do I look like a serial killer in any of these shots? If the answer is yes, then don’t post them.

2. Don’t look like a pretentious douche bag – What does that mean? It depends on the person. Are you standing in front of your flashy Porsche or McMansion in your photos? Are contemplating the universe with the caption to match? Are you holding a pipe while wearing a bow tie made out of pipe cleaners? Looking like a prick is relative to the woman who is viewing your visage. If you use terms like “visage” in your photo captions, you might look like a pretentious douche bag.

3. Don’t use several group photos – Some guys have nothing but group shots. Don’t make a woman search through several photos playing – Where’s Waldo?

4. Don’t cut your head off – I’m going to assume you’re married or hideous. Don’t give me bullshit about having an important job. I once had a date inside the United Nations, it wasn’t the greatest match but his job wasn’t exactly mundane.

5. Don’t use professionally shot modeling or acting photos – They look a bit forced. You can use one or two but don’t have a slew of them.

6. Don’t limit yourself to one photo – Use at least three. The more you show the more likely someone will respond. If your only photo is of yourself from a far distance, no potential date is going to have any idea what you look like. Use a body shot, a crop of your face and one that’s from the waist up. If you have more than three that’s great but three should be a good start.

7. Don’t use a landscape photo as your main profile picture – Again, I will assume you’re hiding something or married. SHOW YOUR FACE!

8. Please don’t post a dick pic – I said please. I’m begging you not to do it, unless of course it’s a hook-up site or a woman asks specifically to see your junk. An unsolicited dick pic is bad enough, a dick pic as your profile photo is the absolute worst.

9. Don’t post a photo of yourself with an ex – Or really even a sister, a friend or any woman other than maybe your mom. It’s confusing, and distracting. I’m going to be trying to figure out who the woman is, rather than just focusing on you. And for the love of all that’s holy, don’t use a photo of yourself next to your ex, with her face blacked out.

10. Limit or eliminate bathroom selfies – You’ve got a smoking hot bod. You want to show it off. Well come up with a more creative way than a self-portrait taken with your cell phone in the bathroom. You could snap one of you working out, or on the beach. I’ve probably seen 10,000 bathroom selfies at this point. Just don’t do it.

BE HONEST – One of my favorite all time profiles was of a beautiful black man in his late thirties. Half of his photos were in typical attire of oxfords, ties, jeans and slacks. Every other photo was of the same man in full women’s drag complete with wig, makeup, lashes, and padding. He openly admitted he was a cross dresser but was straight and interested in women. I APPLAUD this man for making such a bold move. Sure it might turn off a lot of women, but the perfect woman for him wouldn’t mind at all. There were no secrets and I admired his courage for putting it all out there.

If you follow this basic advice I promise you’ll get more emails on your profile!!! And again, when in doubt have a female friend give it the once over before you publish it! You’d be surprised how much having a woman’s perspective could help you out.

I sometimes think being single in New York City turns a person into an emotional zombie. I don’t say that to insult single New Yorkers as I am single myself. I have noticed though in the past few years that my personality has drastically changed when it comes to dating. I used to get really worked about it, and now I’m a step away from comatose. All emotion has basically been beaten out of me. No one has physically attacked me of course, but any rough edges are now weathered down by a sea of apathy. It’s as if the harshness of the dating scene washes over us like a thousand pieces of sand paper an smooths us down to smooth dullness.

After the first few dates, I blamed myself for being overly emotional or too screwed up from my recent divorce. I was a complete emotional wreck and probably should have taken time off before dating, but it wasn’t just my emotional turmoil that was causing the problem. It was an entire city devoid of authentic emotion. Not everyone, but most men acted like the walking dead, ruled by their genitalia and nothing else. I was far more judgmental of this quality when I started out, then I realized it wasn’t so much a choice as a method of survival. Like a nasty pandemic it spread throughout the whole city, neither gender spared. I heard story after story from my male friends of women who acted the same way. We were all reduced to little more than our zip code, our sexual preferences and lifestyles. I was no longer a woman in my late thirties/early forties but Flatbush, straight, non-smoker with cats. Everything else about me didn’t seem to matter anymore.

What caused this? What turned an entire metropolis into the land of the emotionally dead? Technology hasn’t helped. Even though now we can connect in so many ways, I can honestly say without irony that I’ve had more solicitations for cyber sex than actual physical contact. When once a man might call me on the phone to chat, they now text. Communication reduced to broken phrases and emoticons. Even typing in a complete sentence is too much effort for some. Misunderstandings are common as tone is next to impossible to convey and sarcasm deadly. Dating websites have evolved into hook-up apps that promise little more than one awkward or thrilling evening to cut the boredom.

Eventually I’ve succumbed and became numb myself. It must have been all the bad dates, the dick pics, the requests for immediate sex, the constant same day cancellations, and the judgmental pricks who think taking a train to Brooklyn is just too much to ask. I officially gave up a while ago. I’ve shut down all of my online dating profiles, I can’t even fathom joining tinder. When I do date, which isn’t often, I find myself trying to smother any spark of emotions that are left. I tell myself, don’t react, don’t care, show no weakness and maybe you’ll get through it. Maybe if I’m dead enough, I’ll finally win at this game.

But in some ways my zombie infection is a good thing. I used to put up with so much bad treatment. When I would once make excuses for a man who didn’t text back, I now delete them from my phone. I cut them off and don’t look back. When a man is rude or snobbish about my type of employment he becomes invisible to me. When a guy shrugs his shoulders at taking the Q train out to central Brooklyn, I erase him from my brain. I have in many ways become the person I feared. It’s not that I don’t have empathy for others, it’s just survival. In a city where anyone can walk away and return to instant anonymity negative behavior thrives.

I’m less judgmental of people just snapping and hooking up with the next person who offers. I understand the need for human touch that lies within us all no matter how hard we try to bury it. We try to control it completely but all the pornography and our sexually heightened culture can’t control the need to just be next to someone if for a moment. I’ll shuffle back to my own corner of Gotham and try to smother the beast inside who cries out for more. I let the sea of apathy wash over me again and the numbness is comforting.

The number one article on this blog is simply titled “Dating After Divorce: Why it’s so Difficult in your late Thirties” It’s been read nearly 30,000 times. Nothing else I’ve written comes close to the amount of hits that article gets. It’s certainly not my best or most entertaining piece. It gets a lot of hits because there are so many frustrated people searching for answers.

My younger friends try to empathize, but they have no idea what I go through. When a person is in his or her early twenties, they’re constantly meeting other single people. When they get together their friends a few strangers might end up making out on a couch in the corner. When I go to a social event with folks my age, it’s mostly married couples. While the pairs huddle together to discuss co-op boards, school districts and home renovations, I’m in the corner with the other single gals and gay men swapping sex stories and dick pics. I’m not sure why, but straight single men are rare at such soirees. At the last barbeque a unattached heterosexual man showed up alone, then bragged about his multiple girlfriends.

My married friends really don’t get it. I love them dearly, but they just have no idea what I go through. They wake up next to the same person every day of their lives. They pay bills, worry about the future and plan vacations. They might fight often, they might be at the brink of divorce, they might even romanticize their single years, but they’re still one half of a couple. They know nothing of going to every social gathering alone, buying solo movie tickets, or being set up on horrible dates by well-meaning friends.

One married friend suggested that I change my attitude about dating. He then listed three people who had all gotten remarried after a divorce. I had to point out to him that all three examples were men who had married much younger women. Being single past 35 is difficult for both genders, but the challenges men and women face are different. In two of the examples he gave, the men went on to have more children. My age definitely makes me less attractive to a man who wants kids. When I asked my friend for some examples of women who had remarried in my age range, he had none. He just couldn’t see that my problems with dating are real and not imagined. A simple attitude change was not going to produce age appropriate single men from the sky.

When I go out of my social network most of the interest I get is from men half my age. I try to tell the young ones they won’t understand my sarcasm, my world-weary outlook and my complete lack of shame or social filter. Usually they realize they’d rather be with someone with more of a spark of hope in her eyes rather than the jaded cougar. I don’t blame them.

I want my counterpart. A man who’s had a few of his dreams and aspirations crushed. At least he’ll understand my point of view and understand that life is mostly improvisation. The young ones don’t always get that, and how could they? The roller coasters of romance have knocked people my age around so much they’ve gotten skittish and scared. They’ll pine away for a love they can’t have, complain bitterly about the one who broke their heart and avoid making any type of commitment with a new partner. I do empathize as I’m not much different, but with so much hesitation and apathy it’s hard to get excited about anyone.

So I’ve tried, and I have other things to do with my life than spend all of my free time looking for “the one.”. I’ve accepted that this could be my reality for some years to come. It gets lonely, and there are days when I just want to scream at the top of my lungs and make it stop. Then there are times when I’m so thankful that I’m not responsible for anyone else, I’m in charge of all of my finances and I can paint my bedroom whatever color I want. When I walk by a couple fighting, or listen to a friend rant about their marital problems, I think – I’m free.

When did being in a relationship become the only path to contentment and happiness? Don’t we all know couples who are miserable? Don’t we all have friends and family members who remain in a marriage that is a toxic hell? Don’t we all know men and women who will be with nearly any partner rather than be alone? It’s not the years you’ve put in, but the quality of the partnership. Right now after everything I’ve been through, I can honestly say I know more about myself then I ever did when I was someone’s girlfriend or wife. I’ve discovered more about my strengths and weaknesses in the past 5 years than I did in the first 36. I might not have someone to hold my hand when things get rough, but I also don’t have anyone to pull me down or hold me back. I am responsible for my demise or my success.

I’m single and I might remain so for the rest of my life. I probably won’t have kids. I’ll have no first day of school photos, handmade cards with the word “Mom” scribbled in crayon, or pools of vomit to clean up after an underage drinking binge. I won’t go through the highs and lows of parenthood, and none of this means I am less of a person. A partner and a child do not validate my existence on this planet.

I’m not broken because I’ve been alone for an extended period of time. I am single. This is my life, and there is nothing wrong with me because I choose to live alone, rather than stay in a bad partnership. If two people are happy in a long-term committed relationship it’s a beautiful, wonderful, magical thing, but so is building a future by myself, on my terms and without a toxic partner.

It’s been five years since my marriage completely disintegrated. I found myself suddenly thrust back into the dating pool at age 36. My single friends tried to warn me, but I honestly had no choice. My marriage was dead and there was no saving it. I made every dating mistakes a few times. I’ve evolved from overly emotional, clingy and starry-eyed to cynical, jaded and emotionally bereft. I keep hoping things will get better, but they never improve. I’ve tried online dating to no avail. Most of the guys online never follow through with dates, so I find myself carving out precious time only to resort to sitting in a coffee shop by myself or watching House of Cards on Netflix when my date cancels. You know it’s bad when you think to yourself that doing business is easier than dating in this town. I’ve honestly been treated better in most professional relationships, than I ever have been in romantic ones.

So I’ve devised this list. It pretty much encapsulates what’s become of dating in the city that never sleeps. From what I’ve heard this across the board for men and women of all sexual orientations and gender identifications.

How to Date in NYC

1. Lower your expectations – I’ve gone from thinking “Maybe I’ll get remarried someday” to “Just answer a simple text message, I only sent you one in the past three days.”

2. Become numb – Get rid of all of your highs and lows as they will not serve you.

3. Show no weaknesses – Don’t let on your hopes and fears too soon. Show no signs of insecurity. These things can come later, but since this person probably won’t stick around for any length of time, they don’t need to know any of this. Put your game face on and keep it on.

4. Expect rude behavior – If you send a simple “What’s up?” text, do not expect a response. This is after you’ve been out with the person and seen them check their phone every ten minutes. Expect last minute cancellations, constant excuses for why they aren’t available and angry rants about ex-partners. These are all par for the course.

5. Completely give up on the notion of age appropriate – I’m hit on by men as young as 18 up to around 27 or 28, then the next largest demographic is mid-fifties. I can’t explain this, but I’ve given up trying. I just go with what’s offered.

7. Trust no one – Because we live in a city of strangers, a person has to earn your trust before you just believe anything they tell you. “I had to work” could easily mean – “I was hooking up with one of my other regulars” You might eventually trust your partner, but until then, take what they say with a grain of salt. Note inconsistencies, never assume they are legit.

8. Get used to the phrase – “I’m just so busy” – You’ll say this yourself. But you will also hear it as an excuse for everything.

9. Get used to the phrase – “Oh but you live so far away.” New York City is a big town. We sometimes meet in the middle of this Metropolis in Manhattan. Only later do we realize that a Bronx to Queens commute is just impractical. Although some expect to put in absolutely no effort whatsoever. Basically they will only consider dating you on a regular basis if you live two or three stops away on the same subway line they take every day.

10. Have fun with showing off your dick pic collection, and you’ll get one…trust me you’ll get one. – I don’t know if there is a lesbian or straight woman equivalent, or if this phenomena is as common with every sexual orientation. I only know that straight women and gay men easily collect dick pics and full frontal nudes. I’ve scrolled through dozens in my gay friend’s phones. I’ve gotten several and I never once requested – “Please send me a photo of your cock. Preferably a self-portrait taken with your phone. A bathroom shot would really be something special!” I’ve also gotten requests for photographs of body parts or my mouth wrapped around dildos and various objects. I’ve never complied. Who said romance was dead?

11. Accept your fate as a crazy cat lady/eccentric bachelor. – I know this brings us to eleven. For men I guess the crazy cat lady equivalent is the weirdo eccentric bachelor. We all know a few. The guys who never got married and have that apartment just full of strange things from their youth. It’s small and rent stabilized and they’ve lived there for years. They’ll probably die there but they won’t be eaten by their pet cats, instead someone might stumble upon their mummified corpse after neighbors complain of the smell or they are a final no-show for their eviction in housing court. I hope that’s not my fate, but things aren’t looking so good lately.

Susan, I know you really think you’re helping out young women by encouraging them to nab an eligible bachelor while they’re still in college. Interestingly though the divorce rate is much higher for women who marry for the first time under the age 25. If women actually take your advice they might pick what you think is a brilliant mate, but if they marry him before age 25, they’ll battle the same genius in divorce court later.

Here are your eight reasons why women in New York City can’t get a husband. I know this article was published back in March, but a friend just sent me the link and I felt compelled to respond. I left my husband nearly five years ago, and haven’t had a serious long-term relationship since. You claim to know WHY women like myself are still single, so I’m going to answer each one of your reasons with my own personal experience.

1. We drink too much – I actually don’t drink alcohol often, and do absolutely no drugs. I’m a vegetarian and you would probably encourage me to seem less complicated and start eating meat. Well that’s not going to happen.

2. We spend too much time on iphones and other electronic devices – My ipod has been broken for the past several months. I miss it. The earbuds drowned out the constant cat calls. I live in a less gentrified area of Brooklyn, and it never stops. Am I supposed to stop and engage an intoxicated gentlemen the next time he makes a comment about my ass? Maybe that’s why I’m not meeting Mr. Right!

3. We wear too much black – Of course that’s it. Black makes us look like witches and men hate witches. I know Angelina Jolie gets no attention and she wears black all the time. She even plays a witch in Maleficent and everyone knows, men can’t stand the sight of Angelina Jolie.

4. We are dating too many guys at work – I’m self-employed and have no co-workers so I’m not sure how I’m doing that. I guess I’m dating myself too often.

5. We spend too much time with our gay friends – This is New York City, are you out of your mind? I don’t just have gay friends. I’ve got transgender, gay, bisexual, pansexual, polyamorous and several who identify as gender-flexible. I’m not giving up my non-heterosexual friends.

6. We are ignoring our biological clocks – I know I’m 41 and am well aware of it. Am I supposed to get pregnant by any random man? That would seem a bit reckless. How about I just accept it’s not going to happen and focus on something else. Adopted kids need homes too. I don’t have to grow one in my womb.

7. We hook up too much – OH HOW I WISH THIS WAS TRUE! Honestly I’m fairly picky, I’ve got trust issues, and I just don’t feel safe hooking up with most of the guys who offer it. It’s not their looks so much as its how they treat me. If a guy is rude, I have very little interest in sleeping with him. I also don’t like bad sex, and hookups are like rolling the dice. I don’t know the last time you hooked up with anyone but it can be absolutely dreadful.

8. We overly rely on NYC conveniences – Actually I don’t. Take out is pricy. You also implied this lifestyle is making us fat, but New York City women are some of the fittest in the country. And Susan you are a full-figured gal, I would just celebrate it and stop blaming General Tso’s chicken.

So that’s your eight reasons, and I answered every one of them. Now I have a few questions for you. Susan you’re divorced. How did that go? My divorce pushed me to the brink of madness and into a literal death spiral. I had massive depression, anxiety attacks and suicidal tendencies. I eventually went on antidepressants and anti-anxiety medication. I’m fine now, and drug free but, It was a regular horror show. I’m sure your divorce wasn’t easy. Since marriage is about a 50/50 chance nowadays why would you promote anyone to enter into a legally binding relationship that could end in a catastrophic divorce?

Here are my five reasons, why I doubt I’ll ever say “I do” again.

1. I never want to combine my money with another person – This is the MAIN reason I never want to get married again. I used to work with my husband, and when my marriage fell apart my income evaporated. Now I make my own money and decide how I spend it. It’s amazingly liberating and I never want to go back to even a joint checking account.

2. I don’t want to move – I like living in Brooklyn. If I choose to move, it should be my choice.

3. I’ve accepted I’m never having my own children. – If I do decide to have a child, I’ll probably adopt. The adoption process is long and expensive but having a baby at my age is not without problems. I’ve also accepted that I might never be a parent. A lot of women never want to have kids. I did, but my life didn’t work out as planned. I don’t feel like a failure because I won’t be a parent.

4. I feel complete and fulfilled as a single person – I know this might shock you. I don’t know how you manage as a single person yourself. The daily torment must be getting to you. You must be so miserable that you write books encouraging young women to desperately get what you don’t have. I would love to date someone special but the longer I’ve been single the more I’ve grown to love it.

5. I never want to get divorced again – If someone wants to get married four or five times good for them. The prospect of going through another divorce though is so terrifying to me, I think I’ll avoid doing it again.